Literature DB >> 23476599

(2E)-1-(2-Methyl-4-phenyl-quinolin-3-yl)-3-(3-methyl-thio-phen-2-yl)prop-2-en-1-one.

R Prasath1, P Bhavana, Seik Weng Ng, Edward R T Tiekink.   

Abstract

In the title compound, C24H19NOS, the quinoline residue (r.m.s. deviation = 0.018 Å) is essentially orthogonal to both the phenyl [dihedral angle = 88.95 (8)°] and 2-thienyl [81.98 (9)°] rings. The carbonyl O atom lies to one side of the quinoline plane, the carbonyl C atom is almost coplanar and the remaining atoms of the chalcone residue lies to the other side, so that overall the mol-ecule has an L-shape. The conformation about the ethyl-ene bond [1.340 (2) Å] is E. In the crystal, a supra-molecular chain with the shape of a square rod aligned along the b-axis direction is sustained by C-H⋯π inter-actions, the π-systems being the heterocyclic rings.

Entities:  

Year:  2013        PMID： 23476599      PMCID： PMC3588408          DOI： 10.1107/S1600536813004753

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background details and the biological application of quinoline and quinoline chalcones, see: Joshi et al. (2011 ▶); Prasath & Bhavana (2012 ▶); Kalanithi et al. (2012 ▶); Prasath et al. (2013 ▶). For the structure of the dimethyl-substituted quinolinyl compound without a methyl substituent on the 2-thienyl ring, see: Prasath et al. (2011 ▶).

Experimental

Crystal data

C24H19NOS M = 369.46 Triclinic, a = 10.0815 (7) Å b = 10.2956 (7) Å c = 10.5403 (7) Å α = 71.013 (6)° β = 78.697 (5)° γ = 70.412 (6)° V = 969.99 (11) Å3 Z = 2 Mo Kα radiation μ = 0.18 mm−1 T = 295 K 0.40 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.780, T max = 1.000 8430 measured reflections 4473 independent reflections 3484 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.135 S = 1.03 4473 reflections 246 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.26 e Å−3 Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004753/hb7043sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004753/hb7043Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813004753/hb7043Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C24H19NOSZ = 2
Mr = 369.46F(000) = 388
Triclinic, P1Dx = 1.265 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0815 (7) ÅCell parameters from 2781 reflections
b = 10.2956 (7) Åθ = 3.1–27.5°
c = 10.5403 (7) ŵ = 0.18 mm−1
α = 71.013 (6)°T = 295 K
β = 78.697 (5)°Prism, colourless
γ = 70.412 (6)°0.40 × 0.20 × 0.10 mm
V = 969.99 (11) Å3
Agilent SuperNova Dual diffractometer with an Atlas detector4473 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3484 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.025
Detector resolution: 10.4041 pixels mm-1θmax = 27.6°, θmin = 3.1°
ω scanh = −12→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)k = −13→13
Tmin = 0.780, Tmax = 1.000l = −12→13
8430 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0573P)2 + 0.2365P] where P = (Fo2 + 2Fc2)/3
4473 reflections(Δ/σ)max < 0.001
246 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
S10.33532 (6)0.72592 (6)0.97283 (5)0.05153 (17)
O10.33453 (18)0.20079 (15)1.00072 (14)0.0629 (4)
N10.08222 (15)0.34043 (16)0.65204 (16)0.0454 (4)
C10.18240 (18)0.31032 (18)0.54916 (17)0.0399 (4)
C20.1367 (2)0.3073 (2)0.4323 (2)0.0527 (5)
H20.04060.32850.42620.063*
C30.2316 (3)0.2738 (2)0.3286 (2)0.0602 (5)
H30.20020.27180.25220.072*
C40.3757 (2)0.2425 (3)0.3361 (2)0.0608 (6)
H40.43970.21960.26450.073*
C50.4241 (2)0.2449 (2)0.44696 (19)0.0511 (5)
H50.52080.22410.45020.061*
C60.32869 (18)0.27881 (17)0.55698 (17)0.0379 (4)
C70.37112 (17)0.28190 (17)0.67702 (17)0.0363 (4)
C80.26889 (17)0.31240 (17)0.77857 (17)0.0367 (4)
C90.12435 (18)0.33970 (19)0.76224 (19)0.0432 (4)
C100.0110 (2)0.3675 (3)0.8747 (2)0.0672 (6)
H10A−0.08020.39050.84450.101*
H10B0.01640.44660.90080.101*
H10C0.02440.28330.95050.101*
C110.52458 (17)0.24958 (18)0.69071 (16)0.0377 (4)
C120.6053 (2)0.1100 (2)0.7428 (2)0.0514 (5)
H120.56340.03610.77170.062*
C130.7480 (2)0.0793 (2)0.7525 (2)0.0561 (5)
H130.8016−0.01510.78740.067*
C140.8112 (2)0.1878 (2)0.71062 (19)0.0520 (5)
H140.90740.16660.71620.062*
C150.7321 (2)0.3266 (2)0.6608 (2)0.0526 (5)
H150.77450.40020.63340.063*
C160.5892 (2)0.3582 (2)0.65095 (19)0.0467 (4)
H160.53600.45310.61740.056*
C170.30768 (19)0.31202 (19)0.90990 (18)0.0415 (4)
C180.30830 (19)0.44686 (19)0.92575 (18)0.0416 (4)
H180.33530.44531.00590.050*
C190.27227 (18)0.57334 (18)0.83162 (17)0.0391 (4)
H190.24630.57210.75220.047*
C200.26953 (18)0.71087 (18)0.84036 (17)0.0385 (4)
C210.2191 (2)0.84246 (19)0.75107 (18)0.0454 (4)
C220.2355 (2)0.9534 (2)0.7922 (2)0.0590 (5)
H220.20711.04970.74350.071*
C230.2960 (3)0.9070 (2)0.9081 (2)0.0606 (6)
H230.31410.96700.94800.073*
C240.1539 (3)0.8692 (3)0.6258 (2)0.0666 (6)
H24A0.20320.79360.58430.100*
H24B0.16040.95950.56440.100*
H24C0.05630.87150.64840.100*
U11U22U33U12U13U23
S10.0653 (3)0.0586 (3)0.0420 (3)−0.0270 (3)−0.0072 (2)−0.0187 (2)
O10.0963 (12)0.0451 (8)0.0471 (8)−0.0234 (8)−0.0149 (8)−0.0052 (6)
N10.0385 (8)0.0491 (9)0.0537 (9)−0.0144 (7)−0.0028 (7)−0.0203 (7)
C10.0421 (9)0.0381 (9)0.0429 (9)−0.0148 (7)−0.0045 (7)−0.0126 (7)
C20.0524 (11)0.0573 (12)0.0557 (11)−0.0191 (10)−0.0130 (9)−0.0178 (10)
C30.0766 (15)0.0704 (14)0.0451 (11)−0.0282 (12)−0.0101 (10)−0.0222 (10)
C40.0661 (14)0.0750 (15)0.0488 (11)−0.0261 (12)0.0074 (10)−0.0290 (11)
C50.0475 (10)0.0645 (12)0.0479 (10)−0.0219 (10)0.0050 (9)−0.0245 (9)
C60.0401 (9)0.0364 (8)0.0404 (9)−0.0156 (7)−0.0011 (7)−0.0120 (7)
C70.0380 (8)0.0321 (8)0.0412 (9)−0.0137 (7)−0.0025 (7)−0.0108 (7)
C80.0396 (9)0.0345 (8)0.0392 (8)−0.0135 (7)−0.0007 (7)−0.0135 (7)
C90.0381 (9)0.0454 (10)0.0493 (10)−0.0135 (8)0.0028 (8)−0.0199 (8)
C100.0439 (11)0.1004 (18)0.0656 (14)−0.0208 (12)0.0099 (10)−0.0432 (13)
C110.0366 (9)0.0420 (9)0.0371 (8)−0.0139 (7)−0.0011 (7)−0.0134 (7)
C120.0469 (10)0.0448 (10)0.0613 (12)−0.0176 (9)−0.0012 (9)−0.0114 (9)
C130.0451 (11)0.0522 (12)0.0639 (13)−0.0066 (9)−0.0087 (9)−0.0128 (10)
C140.0379 (9)0.0735 (14)0.0508 (11)−0.0182 (10)−0.0040 (8)−0.0239 (10)
C150.0509 (11)0.0640 (13)0.0551 (11)−0.0318 (10)−0.0013 (9)−0.0194 (10)
C160.0476 (10)0.0449 (10)0.0523 (11)−0.0189 (8)−0.0074 (8)−0.0129 (8)
C170.0421 (9)0.0416 (9)0.0419 (9)−0.0136 (8)0.0001 (7)−0.0142 (8)
C180.0449 (9)0.0446 (10)0.0395 (9)−0.0130 (8)−0.0047 (7)−0.0171 (8)
C190.0414 (9)0.0427 (9)0.0380 (9)−0.0134 (8)−0.0026 (7)−0.0172 (7)
C200.0397 (9)0.0426 (9)0.0374 (8)−0.0139 (7)0.0003 (7)−0.0170 (7)
C210.0489 (10)0.0430 (10)0.0456 (10)−0.0133 (8)−0.0019 (8)−0.0157 (8)
C220.0767 (14)0.0408 (10)0.0626 (13)−0.0196 (10)−0.0046 (11)−0.0173 (9)
C230.0802 (15)0.0572 (12)0.0616 (13)−0.0354 (12)0.0030 (11)−0.0293 (11)
C240.0771 (15)0.0589 (13)0.0609 (13)−0.0090 (12)−0.0250 (12)−0.0138 (11)
S1—C231.698 (2)C11—C161.389 (2)
S1—C201.7281 (17)C12—C131.382 (3)
O1—C171.217 (2)C12—H120.9300
N1—C91.310 (2)C13—C141.376 (3)
N1—C11.368 (2)C13—H130.9300
C1—C61.413 (2)C14—C151.366 (3)
C1—C21.410 (3)C14—H140.9300
C2—C31.358 (3)C15—C161.384 (3)
C2—H20.9300C15—H150.9300
C3—C41.390 (3)C16—H160.9300
C3—H30.9300C17—C181.453 (2)
C4—C51.362 (3)C18—C191.340 (2)
C4—H40.9300C18—H180.9300
C5—C61.412 (2)C19—C201.439 (2)
C5—H50.9300C19—H190.9300
C6—C71.426 (2)C20—C211.370 (3)
C7—C81.370 (2)C21—C221.413 (3)
C7—C111.495 (2)C21—C241.494 (3)
C8—C91.423 (2)C22—C231.345 (3)
C8—C171.509 (2)C22—H220.9300
C9—C101.505 (2)C23—H230.9300
C10—H10A0.9600C24—H24A0.9600
C10—H10B0.9600C24—H24B0.9600
C10—H10C0.9600C24—H24C0.9600
C11—C121.381 (3)
C23—S1—C2091.61 (10)C13—C12—H12119.7
C9—N1—C1118.32 (15)C14—C13—C12120.29 (19)
N1—C1—C6122.78 (16)C14—C13—H13119.9
N1—C1—C2118.05 (16)C12—C13—H13119.9
C6—C1—C2119.15 (16)C15—C14—C13119.83 (18)
C3—C2—C1120.68 (19)C15—C14—H14120.1
C3—C2—H2119.7C13—C14—H14120.1
C1—C2—H2119.7C14—C15—C16120.21 (17)
C2—C3—C4120.30 (19)C14—C15—H15119.9
C2—C3—H3119.9C16—C15—H15119.9
C4—C3—H3119.9C15—C16—C11120.58 (18)
C5—C4—C3120.85 (19)C15—C16—H16119.7
C5—C4—H4119.6C11—C16—H16119.7
C3—C4—H4119.6O1—C17—C18121.50 (17)
C4—C5—C6120.50 (18)O1—C17—C8119.87 (15)
C4—C5—H5119.8C18—C17—C8118.60 (15)
C6—C5—H5119.8C19—C18—C17123.79 (16)
C1—C6—C5118.52 (16)C19—C18—H18118.1
C1—C6—C7117.62 (15)C17—C18—H18118.1
C5—C6—C7123.85 (16)C18—C19—C20126.93 (16)
C8—C7—C6118.51 (15)C18—C19—H19116.5
C8—C7—C11121.58 (15)C20—C19—H19116.5
C6—C7—C11119.90 (14)C21—C20—C19127.31 (16)
C7—C8—C9119.67 (16)C21—C20—S1111.30 (13)
C7—C8—C17120.94 (15)C19—C20—S1121.39 (13)
C9—C8—C17119.35 (15)C20—C21—C22111.32 (18)
N1—C9—C8123.07 (15)C20—C21—C24125.56 (17)
N1—C9—C10116.42 (16)C22—C21—C24123.12 (18)
C8—C9—C10120.50 (17)C23—C22—C21113.90 (19)
C9—C10—H10A109.5C23—C22—H22123.1
C9—C10—H10B109.5C21—C22—H22123.1
H10A—C10—H10B109.5C22—C23—S1111.86 (15)
C9—C10—H10C109.5C22—C23—H23124.1
H10A—C10—H10C109.5S1—C23—H23124.1
H10B—C10—H10C109.5C21—C24—H24A109.5
C12—C11—C16118.55 (16)C21—C24—H24B109.5
C12—C11—C7120.36 (15)H24A—C24—H24B109.5
C16—C11—C7121.08 (16)C21—C24—H24C109.5
C11—C12—C13120.52 (17)H24A—C24—H24C109.5
C11—C12—H12119.7H24B—C24—H24C109.5
C9—N1—C1—C6−0.1 (3)C8—C7—C11—C16−90.2 (2)
C9—N1—C1—C2178.26 (16)C6—C7—C11—C1691.0 (2)
N1—C1—C2—C3−178.02 (18)C16—C11—C12—C13−1.3 (3)
C6—C1—C2—C30.4 (3)C7—C11—C12—C13178.36 (18)
C1—C2—C3—C4−0.3 (3)C11—C12—C13—C140.3 (3)
C2—C3—C4—C5−0.1 (3)C12—C13—C14—C150.8 (3)
C3—C4—C5—C60.3 (3)C13—C14—C15—C16−0.7 (3)
N1—C1—C6—C5178.14 (16)C14—C15—C16—C11−0.3 (3)
C2—C1—C6—C5−0.2 (2)C12—C11—C16—C151.3 (3)
N1—C1—C6—C7−1.3 (2)C7—C11—C16—C15−178.31 (17)
C2—C1—C6—C7−179.58 (15)C7—C8—C17—O1−87.5 (2)
C4—C5—C6—C1−0.1 (3)C9—C8—C17—O190.2 (2)
C4—C5—C6—C7179.22 (17)C7—C8—C17—C1894.1 (2)
C1—C6—C7—C81.2 (2)C9—C8—C17—C18−88.2 (2)
C5—C6—C7—C8−178.19 (16)O1—C17—C18—C19−176.33 (18)
C1—C6—C7—C11−179.93 (15)C8—C17—C18—C192.0 (3)
C5—C6—C7—C110.7 (2)C17—C18—C19—C20179.62 (16)
C6—C7—C8—C90.1 (2)C18—C19—C20—C21−172.65 (18)
C11—C7—C8—C9−178.75 (15)C18—C19—C20—S17.9 (3)
C6—C7—C8—C17177.80 (14)C23—S1—C20—C21−0.25 (14)
C11—C7—C8—C17−1.1 (2)C23—S1—C20—C19179.28 (15)
C1—N1—C9—C81.5 (3)C19—C20—C21—C22−179.31 (17)
C1—N1—C9—C10−177.62 (17)S1—C20—C21—C220.2 (2)
C7—C8—C9—N1−1.6 (3)C19—C20—C21—C241.0 (3)
C17—C8—C9—N1−179.27 (15)S1—C20—C21—C24−179.51 (16)
C7—C8—C9—C10177.54 (18)C20—C21—C22—C230.0 (3)
C17—C8—C9—C10−0.2 (3)C24—C21—C22—C23179.70 (19)
C8—C7—C11—C1290.2 (2)C21—C22—C23—S1−0.2 (3)
C6—C7—C11—C12−88.7 (2)C20—S1—C23—C220.24 (17)
D—H···AD—HH···AD···AD—H···A
C4—H4···Cg1i0.932.883.688 (2)146
C22—H22···Cg2ii0.932.603.457 (2)153
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1,C20–C23 and N1,C1,C6–C9 rings, respectively.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C4—H4⋯Cg1i 0.932.883.688 (2)146
C22—H22⋯Cg2ii 0.932.603.457 (2)153

Symmetry codes: (i) ; (ii) .

  3 in total

1.  Spectral, biological screening of metal chelates of chalcone based Schiff bases of N-(3-aminopropyl) imidazole.

Authors:  M Kalanithi; M Rajarajan; P Tharmaraj; C D Sheela
Journal:  Spectrochim Acta A Mol Biomol Spectrosc       Date:  2011-11-23       Impact factor: 4.098

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  (2E)-1-(2,4-Dimethyl-quinolin-3-yl)-3-(thio-phen-2-yl)prop-2-en-1-one.

Authors:  R Prasath; P Bhavana; Seik Weng Ng; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-11
  3 in total

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